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686891

Sigma-Aldrich

Chiralyst P618

Umicore

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Synonym(s):
Pentamethylcyclopentadienylrhodium(III) chloride dimer, Di(μ-chloro)dichlorobis(pentamethylcyclopentadiene)dirhodium(III), 1,3-Cyclopentadiene, 1,2,3,4,5-pentamethyl-, rhodium complex, Bis(dichloro(pentamethylcyclopentadienyl)rhodium), Bis(pentamethylcyclopentadienylrhodium dichloride), Dichloro(pentamethylcyclopentadienyl)rhodium(II) dimer, Tetrachlorobis(pentamethylcyclopentadienyl)dirhodium
Linear Formula:
[Rh(C5Me5)Cl2]2
CAS Number:
12354-85-7
Molecular Weight:
618.08
MDL number:
MFCD00061552
UNSPSC Code:
12161600
PubChem Substance ID:
329761080
NACRES:
NA.22

Quality Level

100

form

powder

reaction suitability

core: rhodium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

SMILES string

Cl[Rh]Cl.Cl[Rh]Cl.C[C]1[C](C)[C](C)[C](C)[C]1C.C[C]2[C](C)[C](C)[C](C)[C]2C

InChI

1S/2C10H15.4ClH.2Rh/c2*1-6-7(2)9(4)10(5)8(6)3;;;;;;/h2*1-5H3;4*1H;;/q;;;;;;2*+2/p-4

InChI key

QNIVKTTWBMFSBR-UHFFFAOYSA-J

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Application

Umicore Precatalysts for Asymmetric and Cross-Coupling Catalysis

Catalyst for:
  • Oxidative olefination reactions
  • C-C bond cleavage of secondary alcohols
  • Ortho C-H olefination of phenol derivatives
  • Oxidative annulation of pyridines
  • Oxidative ortho-acylation of benzamides with aldehydes via direct functionalization of the sp2 C-H bond
  • Amidation reactions
  • Reductive alkylation reactions
Pentamethylcyclopentadienylrhodium(III) chloride dimer can be used as a catalyst for:
  • The synthesis of multiaryl substituted naphthols via dual C-H bond functionalization of 2-aryloxypyridines.
  • Regioselective C-N bond formation of azo compounds, wherein azide acts as a nitrogen source.
  • Annulation of N-benzoylsulfonamide with isocyanide via C-H bond activation.

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Skin Irrit. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Rhodium-Catalyzed Annulation of N-Benzoylsulfonamide with Isocyanide through C-H Activation
Zhu C, et al.
Chemistry?A European Journal , 17(45), 12591-12595 (2011)
Rhodium-Catalyzed Synthesis of Multiaryl-substituted Naphthols via a Removable Directing Group
Wang L, et al.
advanced synthesis and catalysis, 359(21), 3818-3825 (2017)
Rhodium-Catalyzed Synthesis of Multiaryl-substituted Naphthols via a Removable Directing Group
Wang L, et al.
Advanced Synthesis & Catalysis, 359(21), 3818-3825 (2017)
Rhodium-Catalyzed Direct ortho C-N Bond Formation of Aromatic Azo Compounds with Azides
Wang H, et al.
The Journal of Organic Chemistry, 79(7), 3279-3288 (2014)

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